WO2006012779A1 - Extraits de wikstroemia indeca, production de ceux-ci et utilisation de ceux-ci dans la production de produits pharmaceutiques anti-inflammatoires - Google Patents

Extraits de wikstroemia indeca, production de ceux-ci et utilisation de ceux-ci dans la production de produits pharmaceutiques anti-inflammatoires

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Publication number
WO2006012779A1
WO2006012779A1 PCT/CN2004/000907 CN2004000907W WO2006012779A1 WO 2006012779 A1 WO2006012779 A1 WO 2006012779A1 CN 2004000907 W CN2004000907 W CN 2004000907W WO 2006012779 A1 WO2006012779 A1 WO 2006012779A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
diseases
compound
salts
extract
Prior art date
Application number
PCT/CN2004/000907
Other languages
English (en)
Chinese (zh)
Other versions
WO2006012779A8 (fr
Inventor
Susumu Kitanaka
Liyan Wang
Original Assignee
Nihon University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nihon University filed Critical Nihon University
Priority to PCT/CN2004/000907 priority Critical patent/WO2006012779A1/fr
Priority to CN2004800437624A priority patent/CN101014560B/zh
Publication of WO2006012779A1 publication Critical patent/WO2006012779A1/fr
Publication of WO2006012779A8 publication Critical patent/WO2006012779A8/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/83—Thymelaeaceae (Mezereum family), e.g. leatherwood or false ohelo
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/105—Aliphatic or alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
    • C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
    • C07C49/733—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having two rings

Definitions

  • the present invention relates to a genus extract, a preparation method thereof and an application thereof in the preparation of a medicament, and in particular to a compound having an anti-inflammatory effect extracted from a plant. Background technique
  • Daily inflammatory diseases that plague people include joint inflammation such as osteoarthritis, rheumatoid arthritis, rheumatoid arthritis, gout arthritis, etc.; inflammatory skin diseases such as eczema, psoriasis, dermatitis, etc.; inflammatory eye diseases such as Uveitis, conjunctivitis, etc.; pulmonary diseases such as asthma, bronchitis, acute respiratory distress syndrome, etc.; bacteremia, toxemia, aphthous ulcer, gingivitis, pancreatitis, etc.; gastrointestinal diseases such as festivals Segmental ileitis, atrophic gastritis, ulcerative colitis, abdominal inflammation, peptic ulcer, irritable bowel syndrome such as mucosal inflammation caused by H. pylori infection or caused by non-steroidal anti-inflammatory drugs Gastrointestinal diseases and so on.
  • joint inflammation such as osteoarthritis, rheumatoid arthritis, rheumatoid arthritis
  • NO nitric oxide
  • L-arg L-arginine
  • nNOS neuronal NO synthase
  • iN0S inducible NO synthase
  • iNOS lipopolysaccharide
  • Wiks troemia indica CA Mey is distributed in Guangdong, Guangxi, China. Rutaceae plants in Taiwan and other places. It has been used for swelling, pain relief, rheumatism, and tumors very early. The clinical effect of this plant in the treatment of chronic bronchitis and cancer has been affirmed. In the Dictionary of Traditional Chinese Medicine
  • One of the objects of the present invention is to find an effective active compound which can be used for the preparation of an anti-inflammatory drug by analyzing the active ingredient extracted from the king.
  • Another object of the present invention is to provide a method for extracting an active ingredient from a phylum.
  • the invention also provides a compound extracted from the king of the king for preparation: ⁇
  • a compound (1) of the formula (1) which is extracted from the king, and the method for extracting the compound of the active formula (1) from the king of the invention comprises the following steps:
  • step 3) The eluate collected in step 3) is further separated and purified by high pressure liquid chromatography to obtain a compound of the formula (1).
  • concentration under reduced pressure is preferably carried out at 40 °C.
  • Another aspect of the invention provides a compound of formula (1), or a pharmaceutically acceptable salt thereof, Use of an enantiomer, racemate or tautomer in the manufacture of a medicament for the treatment or prevention of a disease in which inhibition of NO production activity is beneficial.
  • Another aspect of the invention provides a compound of formula (1), or a pharmaceutically acceptable salt, enantiomer, racemate, tautomer or physiologically functional derivative thereof, for use in the treatment or prevention of an inflammatory disease Use in the preparation of a drug.
  • Suitable salts include those formed with organic and inorganic acids or bases; pharmaceutically acceptable salts include those formed with hydrochloric acid, hydrobromic acid, sulfuric acid, citric acid, tartaric acid, phosphoric acid, lactic acid, pyruvic acid, acetic acid, Fluoroacetic acid, succinic acid, oxalic acid, fumaric acid, maleic acid, butanone diacid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, benzenesulfonic acid, isethionate; pharmaceutically acceptable basic formula Salts include ammonium salts, alkali metal salts such as sodium and potassium salts, alkaline earth metal salts such as calcium and magnesium salts, and salts with organic bases such as dicyclohexylamine and N-mercapto-D-glucosamine.
  • physiologically functional derivatives include esters, amides, carbamates, preferably esters and amides.
  • the compounds of the invention may also be advantageously administered in combination with a second pharmaceutically active substance, in particular a selective inhibitor of an inducible cyclooxygenase (COX-2) isoenzyme, specifically a compound provided by the invention or a pharmaceutical thereof
  • COX-2 inducible cyclooxygenase
  • Inflammatory diseases and clinical conditions include joint diseases, especially arthritis (such as rheumatoid arthritis, osteoarthritis), or gastrointestinal diseases (such as ulcerative colitis, gastritis, and other infections caused by mucosal inflammation, by Intestinal diseases caused by non-steroidal anti-inflammatory drugs), lung diseases (such as adult respiratory distress, asthma, sputum fibrosis, chronic obstructive pulmonary disease), heart disease (such as myocarditis), neurological diseases (such as multiple Sclerosis), pancreatic diseases (such as diabetes and complications), kidney diseases (such as glomerulonephritis), skin diseases (such as dermatitis, psoriasis, eczema, urticaria), eye diseases (such as glaucoma), transplant disease (eg rejection), multiple organ diseases (eg systemic lupus erythematosus) and inflammatory sequelae following viral and bacterial infections.
  • arthritis such as rheumatoid arthritis, osteoarthritis
  • the compounds provided by the present invention can help prevent or treat lymphocyte loss associated with HIV infection, increase the radiosensitivity of tumor cells during radiotherapy, P tumor growth, tumor development, angiogenesis, and tumor metastasis. .
  • the compounds provided by the present invention can also be used in the preparation of health foods, beverages, or feeds and the like.
  • the method for extracting the active compound in the king of the present invention is simple and practical, and the extracted active compound has a clear structure and has an exact NO inhibitory activity, and has an anti-inflammatory effect without cytotoxicity. detailed description
  • the NO production inhibition activity test was carried out on various extracts (refer to Example 2), and the hexane extract (76, 1%) and ethyl acetate extract were obtained under the conditions of a test sample concentration of 100 g/ml. 86.9%), butanol extract (6 45%), N0 production inhibition rate affirmative;. all extracts were found not to poison fine packet '1' born in the MTT cell toxicity in acetic acid to take the most active.
  • Extract extract fr.2 using silica column (wako gel) C-300, 2.2 ⁇ 22cm) Separation, elution with chloroform:methanol (100: 0-0: 100), concentration and drying under reduced pressure at 40 ° C, yielding 11 (fr.2-1 to fr.2- 11) Elution of the fraction.
  • fr.2 - 3 (1. lg)
  • CHP-20 column (4x 48cra) Separation followed by Elution with 30% methanol, 50% methanol, 70% methanol, methanol gave four fractions: fr. 2-3- A (0.12 g), fr. 2-3-B (0. 65 g), Fr. 2-3-C (0. 03 g ), fr. 2 - 3-D (0. 07 g ). Purification of fr.
  • the inhibitory effect of macrophages on NO production by the stimulation of stems and lipopolysaccharide was obtained by the following real face method. Further, the suppression effect of NO generation was evaluated based on IC50 (urn) which hindered the effect.
  • Naphthylethylenediamine hydrochloride (lg and pure medicine)
  • Lipopolysaccharide (LPS, 055: B5 lOmg, Sigma)
  • RAW264.7 cells (2 plates) in a 50ml Falcon hose.
  • the cells were pelleted by a centrifuge (100 rpm, 3 min, 4 ° C) and the supernatant was removed with a pipette. 10 ml of fresh medium was added to suspend it. The concentration was adjusted to 1, 5 X 10 5 / ml, and injected into a 96-well plate (Sumitomo Electric 8096R) at a rate of 20 ( ⁇ L per well), and the cells were cultured in a C0 2 incubator for 1-2 hours.
  • LPS ( lO g/Ml, Sigma, 055: B5) 2 L, mouse INF- ⁇ (33 ng/raL, Genzyme) 2 ⁇ , sample 0.4 L. Incubate for 16 hours in a CO 2 incubator. Final concentration is INF- ⁇ 0.33 Ng/mK LPS100ng/ml.
  • the sample is dissolved in DMS0, the content of DMS0 relative to the medium is adjusted to 0, 2%. Take the culture supernatant 100, add 0.1% naphthalene diamine solution 50 L, p-aminobenzenesulfonate Amide solution 5 ( ⁇ L, placed in the dark for 10 minutes at room temperature.
  • the absorbance OD of 57 Onm was measured with a spectrophotometer. STD was treated with sodium nitrite solution (100, 50, 20, 10, 5, 2, 1 , 0 um ). For cell survival rate, microscopic observation and MTT assay were performed.
  • Cytotoxicity was determined by MTT assay and microscopic examination.
  • the MTT method is a known conventional method. That is, in a 96-well ⁇ : titration plate, the cell concentration of 200 ⁇ 1 per well is 1.0 ⁇ 10 5 cells/ml, and different concentrations of extract or monomer components are added, the cells are cultured for 16 hours, and MTT reagent is added. Incubate for another 4 hours. The supernatant was discarded, 150 L DMSO was added, and the resulting formazan (f ormazane) was completely dissolved, and the absorbance at 570 nm was measured.
  • X the amount of N0 2 - induced by IFN- ⁇ and LPS in the presence of the test compound, Y; induced N0 2 - in the absence of real-face compound, IFN- ⁇ and LPS the amount,
  • the compound (1) or a pharmaceutically acceptable salt, enantiomer, racemate, tautomer or physiological functional derivative thereof is administered alone, it is preferably provided in a pharmaceutical preparation, and the preparation includes a compound (1) or a pharmaceutically acceptable salt, enantiomer, racemate, tautomer or physiologically functional derivative thereof, a pharmaceutically acceptable carrier or excipient thereof, and optionally one or A variety of other therapeutic ingredients.
  • the preparation includes an orally administered preparation, a parenteral preparation (including intradermal injection, intramuscular injection, intravenous injection, and intra-articular injection), an inhalation preparation (including a pressurized aerosol device, a sprayer, and a different dose).
  • a parenteral preparation including intradermal injection, intramuscular injection, intravenous injection, and intra-articular injection
  • an inhalation preparation including a pressurized aerosol device, a sprayer, and a different dose.
  • Microparticle powders or aerosols produced in insufflators rectal and topical formulations (including dermal, buccal, sublingual, intraocular). Most suitable administration The route depends on the condition and disease of the patient being administered.
  • the formulations are usually provided in unit dosage form and may be prepared by any methods known in the art of pharmacy. All methods include the step of mixing the active ingredient with a carrier which is comprised of one or more accessory ingredients.
  • the active ingredient is uniformly and tightly bound to a liquid or a fine solid carrier or both, and then the product is formulated as needed;
  • the preparation of the present invention suitable for oral administration can be in a separate unit such as a capsule, a flat An elixirs or tablets are provided, and each unit contains a predetermined amount of the active ingredient; a powder or granule; a water-soluble liquid or suspension; or an oil-in-water emulsion or a water-in-oil emulsion; or a granule or a syrup Agent or paste.
  • Tablets may be prepared by tableting or molding, optionally with one or more accessory ingredients; by compressing free-flowing forms such as powders or granules on a suitable machine (optional with binders, lubricants, inert diluents)
  • the active component of the surfactant, or dispersion of the dispersing agent can be used to prepare compressed tablets; the tablets may optionally be coated or indented and formulated to provide sustained or controlled release of the active ingredient.
  • Formulations for parenteral administration include aqueous and non-aqueous sterile injectable solutions, which may contain antioxidants, buffers, antibacterial agents, and solutes, aqueous and non-aqueous sterile suspensions which render the formulation invigorating with the patient's blood.
  • the suspension may contain a suspending agent and a thickening agent; the formulation may be packaged in unit or multi-dose, for example, in a sealed ampoule and vial; and may be stored under lyophilization conditions, prior to use It is only necessary to provide a sterile liquid carrier such as saline or water for injection; the injectable solutions and suspensions may be prepared in the form of powders, granules and various the various compositions described above.
  • Formulations for rectal administration may be presented as a suppository in a conventional carrier such as cocoa butter or polyethylene glycol.
  • Formulations for topical administration to the oral cavity including lozenges of the active ingredient in a flavoring base such as sucrose, arabinose.
  • formulations of the present invention also include other conventional ingredients of the type of preparations known in the art, such as flavoring agents suitable for oral administration and the like.
  • Example 5 preparing food
  • the compound (1) provided by the present invention may also be provided in the form of a food.
  • Preferred food forms include powders, granules, pastes, gelatins and the like, and the granule form may be added with a sugar such as lactose to increase the sweetness;
  • these foods or beverages may also contain vitamins, inorganic elements such as calcium, alcohols, deodorants, such as polyphenols.
  • vitamins, inorganic elements such as calcium, alcohols, deodorants, such as polyphenols.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Immunology (AREA)
  • Polymers & Plastics (AREA)
  • Mycology (AREA)
  • Botany (AREA)
  • Food Science & Technology (AREA)
  • Epidemiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Rheumatology (AREA)
  • Microbiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biotechnology (AREA)
  • Pain & Pain Management (AREA)
  • Medical Informatics (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Nutrition Science (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Transplantation (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne des extraits de Wikstroemia indeca C.A.Mey, un procédé de préparation de ceux-ci et des utilisations pharmaceutiques de ceux-ci, la formule (1) du composé actif extrait.
PCT/CN2004/000907 2004-08-06 2004-08-06 Extraits de wikstroemia indeca, production de ceux-ci et utilisation de ceux-ci dans la production de produits pharmaceutiques anti-inflammatoires WO2006012779A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/CN2004/000907 WO2006012779A1 (fr) 2004-08-06 2004-08-06 Extraits de wikstroemia indeca, production de ceux-ci et utilisation de ceux-ci dans la production de produits pharmaceutiques anti-inflammatoires
CN2004800437624A CN101014560B (zh) 2004-08-06 2004-08-06 了哥王提取物、其制备方法及其在制备抗炎药物中的应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2004/000907 WO2006012779A1 (fr) 2004-08-06 2004-08-06 Extraits de wikstroemia indeca, production de ceux-ci et utilisation de ceux-ci dans la production de produits pharmaceutiques anti-inflammatoires

Publications (2)

Publication Number Publication Date
WO2006012779A1 true WO2006012779A1 (fr) 2006-02-09
WO2006012779A8 WO2006012779A8 (fr) 2007-04-19

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2004/000907 WO2006012779A1 (fr) 2004-08-06 2004-08-06 Extraits de wikstroemia indeca, production de ceux-ci et utilisation de ceux-ci dans la production de produits pharmaceutiques anti-inflammatoires

Country Status (2)

Country Link
CN (1) CN101014560B (fr)
WO (1) WO2006012779A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100463906C (zh) * 2007-03-07 2009-02-25 哈尔滨医科大学附属第二医院 西瑞香素的提取方法
CN102311415A (zh) * 2011-09-29 2012-01-11 广东药学院 一种从了哥王中提取西瑞香素的方法
CN105315147A (zh) * 2014-08-03 2016-02-10 江苏康缘药业股份有限公司 一种愈创木烷型倍半萜类化合物及其制备方法和应用

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101601666B (zh) * 2009-07-10 2011-05-25 暨南大学 了哥王提取物及其制备方法和用途
CN102344454B (zh) * 2011-08-01 2013-11-06 广东药学院 了哥王提取物及其制备方法和应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1252285A (zh) * 1998-10-23 2000-05-10 沈阳药科大学 抗爱滋病新药了哥王提取物的制备方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1252285A (zh) * 1998-10-23 2000-05-10 沈阳药科大学 抗爱滋病新药了哥王提取物的制备方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KE XUEHONG ET AL.: "Pharmacology study on the antiinflammation and analgesia of liao ge wang tablet", LISHIZHEN MEDICINE AND MATERIA MEDICA RES, vol. 114, no. 10, 2003, pages 87 - 92 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100463906C (zh) * 2007-03-07 2009-02-25 哈尔滨医科大学附属第二医院 西瑞香素的提取方法
CN102311415A (zh) * 2011-09-29 2012-01-11 广东药学院 一种从了哥王中提取西瑞香素的方法
CN102311415B (zh) * 2011-09-29 2013-06-26 广东药学院 一种从了哥王中提取西瑞香素的方法
CN105315147A (zh) * 2014-08-03 2016-02-10 江苏康缘药业股份有限公司 一种愈创木烷型倍半萜类化合物及其制备方法和应用

Also Published As

Publication number Publication date
WO2006012779A8 (fr) 2007-04-19
CN101014560A (zh) 2007-08-08
CN101014560B (zh) 2010-04-28

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